N,N'-Dimethylthiourea → 2-Methylimino-3-methyl-5-t-butyl-tetrahydro-1,3,5-thiadiazin-4-one

HRID 237073Notes

Reaction equation

HRID 237073 reaction equation
[C:1]([N:5]([CH2:9]Cl)[C:6](Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:11][NH:12][C:13]([NH:15][CH3:16])=[S:14]>C1(C)C=CC=CC=1>[CH3:11][N:12]=[C:13]1[N:15]([CH3:16])[C:6](=[O:7])[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][S:14]1

Participants

4

Reactant 2

HCID 2723631N,N'-DimethylthioureaHCID 21314703N-t-butyl-N-chloromethylcarbamoyl chloride

Product 1

HCID 213147402-Methylimino-3-methyl-5-t-butyl-tetrahydro-1,3,5-thiadiazin-4-oneYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 50 ml of toluene, were dissolved 3.7 g (0.02 mole) of N-t-butyl-N-chloromethylcarbamoyl chloride and 2.0 g (0.02 mole) of 1,3-dimethylthiourea. The solution was heated under reflux with stirring for one hour. After cooling, the precipitated crystals (m.p. >220° C. decomp.) were collected by filtration, washed with a small quantity of acetone, dissolved again in 100 ml of water, admixed with 10 ml of a 20% sodium hydroxide solution, and extracted with 50 ml of benzene. The benzene layer was dried and concentrated under reduced pressure to obtain 3.5 g (83% yield) of crystals melting at 51°-52° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals (m.p. >220° C. decomp.) were collected by filtration
  5. washwashed with a small quantity of acetone
  6. dissolutiondissolved again in 100 ml of water
  7. extractionextracted with 50 ml of benzene
  8. dry with materialThe benzene layer was dried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1e14114cecc466f8a0db06299925de7
Source dataset
uspto-grants-1979_06
Patent number
US04159328

Reaction notes

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